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When Jay and I were in Iceland late June/early July of 2012, I discovered I’d finally accumulated enough miles via my Chase Sapphire Preferred card to book our dream trip to Hawaii. We were effectively on one vacation and planning another.

Our excitement was through the roof. I booked us from JFK-SFO-OGG on January 10 and HNL-LAX-JFK on January 20th.

Ten days in Hawaii. Total out-of-pocket cost: $15. To book the award ticket was just $7.50 a person.

There was only a little drama. I ended up redepositing the miles and outright buying a flight from SFO-LAX-HNL on Delta because it was so cheap that I was no longer getting my .02 per mile – pretty much the only policy I hold when it comes to redemption values. But we kept the JFK-SFO leg on United.

The big day finally rolled around. It was balmy in New York, but certainly not beach weather. We woke up early to take the A train to Howard Beach, then the AirTrain to the terminal at JFK. It was one of those moments where the plane was boarding, the door would soon be closed, and we were still in the security line. It was the first time I ran through the airport in my socks. We found our seats on the plane, which was surprisingly empty. Economy seats we had. There were plenty of business and first seats available, but we had to suck it up and sit in the back of the plane. But we didn’t care. We were embarking on the first leg of our trip to Hawaii.

Flying over Colorado? Wyoming?

When we got to SFO, we had to change terminals, which was actually pretty easy. The only thing that sucked was having to grab our bags and recheck them. There was no SkyClub in SFO (!) but we only had time to grab a quick sandwich and then it was time to board our Delta flight to LAX.

Thanks, Deltoid

Once at LAX, we had a few hours to kill, so we hung out in the SkyClub, where I concocted a brilliant new drink: ginger ale and rum with a splash of grenadine. I had two. NOM!

Impromptu mixology

I worked on my laptop and watched the sunset over the ocean from inside the terminal.

Sunset at LAX

LAX-OGG was our third flight that day. The two before were nothing special. Economy, standard service, no food, alright seats. Small regional jet from SFO-LAX. The plane to OGG was huge though, and completely full. It always breaks my heart to watch the boarding process of a large aircraft. Oh my fuck, people are so stupid.

I chose Delta as my airline of choice for my $200 airline credit benefit with my American Express Platinum card, so treated myself and Jay to some drinks and food for purchase. We were obviously on a flight that held many attendants of a destination wedding. People were getting plastered and were so loud. Since it was a late flight, people finally konked out after about 90 minutes.

I managed to get a wink or two, and when I woke up, we were a little over an hour from OGG. I was beyond thrilled. When I saw the first flickers of lights on the ground, I knew we were close. Flying over the ocean at night is terribly boring. But the long day of flights was finally over. We were in Maui. The flight attendants made an announcement wishing everyone a pleasant wedding. We did not get lei’d.

MAUI

It was 11pm when we landed. We dashed off the plane, stretched our legs, and went to grab our bags. I was immediately struck that the airport was all open-air (they all are in Hawaii, I found out). The light jacket I was wearing was too much. It was WARM. YES.

Love that shirt!

We went out to find a taxi and were immediately scolded for jaywalking. Um, this definitely wasn’t New York. It was actually really hard to find someone who would accept a credit card as payment. Again, very NOT New York. Also, there were a lot of women taxi drivers. We finally found a lady who would accept cards. I want my Ultimate Rewards points! By this time, we were halfway delirious and wanted to be in our room ASAP.

She drove us the twenty minutes to our hotel, the Aston Maui Li in Kihei, HI that I booked using ~47,000 United miles. We got our bags, and wanted to leave tip on the credit card. She demanded the tip in cash. Jay gave her all he had, which was about $6 (still a good tip for a $20 cab ride). She glared at us as we wheeled our bags away. It was so weird. But whatever.

We went to the checkin desk where the front desk employee was EXTREMELY thorough about the property. We were both so tired that we nodded off a bit during his spiel. I perked up when he said he’d upgraded us to an Ocean View room for free. The words “free upgrade” could pull me out of a deep REM cycle, I swear.

The room was basic, but we could indeed see the ocean. It was night, we were exhausted, and we looked forward to seeing Hawaii in the morning sunshine.

The next day we got the full effect. The property, the palm trees and beaches, the ocean… it was all perfect. We spent four days lying on the beaches to recover and reenergize. Maui was amazing. The beaches were wonderful, and we got quite a nice base tan.

Right outside our room

Our beach on Maui

Hang loose

There were lots of handgliders during the day on the beach. In the mornings, we had breakfast at a cafe down the street, and in the evenings we explored a few different restaurants including the most amazing taco place I’ve ever been to in my life. The fish tacos were so flavorful and fresh. YUM.

We heard of a couple of gay places on Maui. First, the Sunseeker Resort is a gay owned and operated facility, and is apparently clothing optional. We walked by on the way to a sushi place, but didn’t see any nudity. :p

Then, there is a gay nude beach called Little Beach. It is only accessible by car. Since we didn’t rent one for this leg of the trip, we missed out on the chance to get some sun on our blindingly white backsides.

Let’s face it, I went to Hawaii for the Mai Tais

What I wore to the luau

Sunset over Maui

Then, on January 14th, we flew to Hilo. We took a different car service to the Maui airport.

HAWAII (THE BIG ISLAND)

The big island was all Airbnb and Pointshound finds. We got some great deals, averaging about $60/night. We picked up a rental car from National, booked through Ultimate Rewards for only $167 for three days, and drove to our first Airbnb in Pahoa, HI.

Black sand beach on Hawaii

Waves crashing over black lava beaches

I was immediately struck by vast change in geology. The black sand beaches were rugged, and breathtaking.

Our Airbnb host was charming and kind, but we only stayed in each place for one evening. The next day, we drove north on the Hawaii Belt Road, all the way to Kona. The plan was to completely circumnavigate the island. Along the way, we saw Akaka Falls, more stunning beaches, and so much lush vegetation. We also grabbed a delicious lunch at a bakery/cafe and stopped to stretch our legs, and visit a few scenic points.

Very rugged. Uh oh!

Northern tip of the Big Island – it looks like Wisconsin

The change is geography was dramatic. In the higher altitudes, it was extremely foggy, and sometimes rainy. By the time we made it to Kona, it was sunny and gorgeous again. The western side of the island is very rocky and rugged, with lots of lava fields. We did make it to one coffee plantation near Kona, though.

Coffee plantation in Kona, Hawaii

That night, we tried to sample Kona’s gay scene, but me and Jay ended up at a bar with one other guy and a very eager bartender. Not so great. Maybe we didn’t hit up the right place(s). We were exhausted anyway, and went to sleep in our gorgeous Airbnb rental with a view of the ocean beyond the city of Kona.

The next day, we drove to Volcano to see some of the hot magma and even more lava. What we saw, I will never forget for the rest of my life. Pictures don’t do it justice. It was a complete sensory experience. I could not only see it, but hear the crackle and force, smell the sulphur, and feel the vibration of the earth. Completely stunning.

I highly recommend a visit to Volcano if you are at all interested in geography/geology, or just want to experience the power of the earth.

Pele was raging

Mist and fog filled the air all around the volcano

We stayed that night at a creepy BnB we found on Pointshound. The woman was very religious, and the decorations were horrible. It was called End of Road Bed and Breakfast. Yeah, um… if you’re a fellow gay traveler, AVOID. We did have a fantastic dinner with lovely cocktails at the main lodge in Volcano. We wished we’d opted to stay there instead. Live and learn!

The next day, we returned the car and flew to Oahu.

OAHU

We were supposed to stay with one of my college friends on Oahu, but she screwed us over so we had to make last-minute Airbnb accomodations. Luckily, they were fine. We booked another car rental for pickup at HNL, this time with Budget. It was only $125 for three days.

We were most looking forward to our stay at the Hilton Waikiki Village. In the meantime, we partied with the gays in Honolulu, stayed out till four in the morning, and got drunk for $15 at a great little bar called Bacchus. Honolulu was very gay-friendly.

Dramz in Honolulu

The next day, we explored Honoruru.

Honoruru

We went to check into the Hilton, which I booked through American Express Fine Hotels & Resorts. It offered me a whole slew of upgrades, including early checkin, late checkout, room upgrade, free breakfast, and a $100 food and beverage credit to use in the resort.

When we finally found the checkin desk which took forever as the place is very poorly signed, I heard those magical words again. “Free upgrade.” But this time, we snagged ourselves an Ocean View Suite. It had a separate sitting area, a huge king sized bed, and a large bathroom filled with sweet-smelling coconut- and pineapple-based products. We were shown to our room by the Concierge, who made us feel very welcomed. He brought along a kit detailing all of our amenities.

Our suite

View of the Pacific from the balcony

Thanks, Hilton and Amex!

We definitely used our food and beverage credit!

Kissing penguins at the Hilton

The next day, we laid on next to the beach until about 3pm and sipped Mai Tais. Then, we came in, showered, and packed up our things. The Hilton was wonderful! Five out of five stars.

Then, for our last day/evening in Hawaii, we had lunch at a little cafe downtown and dinner at an Italian restaurant further east, and drove around Oahu. We went down to Diamondhead and hiked down to the beach. There was supposed to be a gay beach down there, but all we could see was families with small children. We gave up and laid out to get a few last rays of sun.

Last day on Oahu

All-in-all, a wonderful trip. A few observations:

Hawaii was way more religious than I expected. There were churches EVERYWHERE

The weather was perfect (that might warrant a DUH)

I felt very comfortable the entire time. Everyone was kind

Hawaiians LOVE Spam

It was no more expensive than anything in NYC

I would totally go back again. I think Maui was my fave! (Then the Big Island, then Oahu.)

They love it!

Bottom line

Couldn’t have asked for a better trip. Read this post to find out how I made this dream a reality. We only paid $100 per day between the two of us for hotels, car rentals, food, gas, souvenirs, AND R/T flights from New York.

This trip was my first points redemption. Safe to say I’m completely hooked!

Doesn’t have to be!

Hot dogs at HNL – back to NYC

The flights back to New York were standard. We hung out in the nice SkyClub at HNL and had a couple of beers. When we got to LAX, we saw all members of the Boy Band 98 Degrees at the SkyClub. They were in business, of course. Jay and I were upgraded to Economy Comfort, which was a nice gesture. I sat right next to the door, and was the first person off the plane.

Fenwick was VERY happy to see us when we got back home to Brooklyn. I slept for a solid 12 hours to recoup from a long day of travel. A few days later, it snowed and was blisteringly cold, but I still had Hawaii on my mind as I geared up for my next trip to Madrid.

Before that, my credit history was full of collections, defaults, and charge-offs. My credit score was in the low 500s.

In early 2012, I resolved to finally get my credit under control. I used my tax return (in conjunction with my full-time job at the time) to pay down my credit cards to $0. I started making big payments at the end of January.

By late February, my credit score shot up to 702! Pretty amazing – but was I ready to apply for a premium card?

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Harlan Vaughn

Hello and welcome to Out and Out! My name is Harlan – I’m a points and miles enthusiast who loves to travel. I am interested in personal finance, the power of positive thinking, and the extraordinary journeys that make life worth living.
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